Trifluoroacetic acid → Methyl 4-(1-carboxyvinyl)-2,3,5,6-tetrafluorobenzoate

HRID 981263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 981263
C1(C(C2C=CC=CC=2)[O:8][C:9]([C:11]([C:13]2[C:22]([F:23])=[C:21]([F:24])[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:15]([F:25])[C:14]=2[F:26])=[CH2:12])=[O:10])C=CC=CC=1.FC(F)(F)C(O)=O.CCCCCC.C(=O)([O-])O.[Na+]>C1(OC)C=CC=CC=1>[C:9]([C:11]([C:13]1[C:14]([F:26])=[C:15]([F:25])[C:16]([C:17]([O:19][CH3:20])=[O:18])=[C:21]([F:24])[C:22]=1[F:23])=[CH2:12])([OH:10])=[O:8]

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 516892Sodium BicarbonateHCID 15136249Methyl 4-(1-diphenylmethoxycarbonylvinyl)-2,3,5,6-tetrafluorobenzoate

Produkt 1

HCID 15136251Methyl 4-(1-carboxyvinyl)-2,3,5,6-tetrafluorobenzoateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7519AnisoleLösungsmittel

Versuchsvorschrift

In 15 ml of anisole was dissolved 3.2 g of methyl 4-(1-diphenylmethoxycarbonylvinyl)-2,3,5,6-tetrafluorobenzoate. To the resulting solution was added 15 ml of trifluoroacetic acid. The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure. The residue obtained was mixed with 20 ml of n-hexane. The resulting mixture was adjusted to pH 7.5 with a saturated aqueous sodium hydrogencarbonate solution. The aqueous layer was separated and mixed with 50 ml of ethyl acetate. The resulting mixture was adjusted to pH 1 with 6N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 1.9 g (yield: 95.0%) of methyl 4-(1-carboxyvinyl)-2,3,5,6-tetrafluorobenzoate.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue obtained
  3. customThe aqueous layer was separated
  4. additionmixed with 50 ml of ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3001b803c87c4ce3aaec23c772ddbb92
Quelldatensatz
uspto-grants-1991_02
Patentnummer
US04990508

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